Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi. Issue 6 (10th April 2018)

• Record Type: Journal Article
• Authors: Klas, Kimberly R.; Kato, Hikaru; Frisvad, Jens C.; Yu, Fengan; Newmister, Sean A.; Fraley, Amy E.; Sherman, David H.; Tsukamoto, Sachiko; Williams, Robert M.
• Is Part Of: Natural product reports. Volume 35:Issue 6(2018)
• Page Start: 532
• Page End: 558
• Publication Date: 2018-04-10
• Subjects: Natural products -- Periodicals; Produits naturels -- Périodiques; 547.7
• DOI: 10.1039/c7np00042a
• Languages: English
• ISSNs: 0265-0568

Abstract

Abstract : Various fungi of the genera Aspergillus, Penicillium, and Malbranchea produce prenylated indole alkaloids possessing a bicyclo[2.2.2]diazaoctane ring system. Abstract : Covering: up to February 2017 Various fungi of the genera Aspergillus, Penicillium, and Malbranchea produce prenylated indole alkaloids possessing a bicyclo[2.2.2]diazaoctane ring system. After the discovery of distinct enantiomers of the natural alkaloids stephacidin A and notoamide B, from A. protuberus MF297-2 and A. amoenus NRRL 35660, another fungi, A. taichungensis, was found to produce their diastereomers, 6- epi -stephacidin A and versicolamide B, as major metabolites. Distinct enantiomers of stephacidin A and 6- epi -stephacidin A may be derived from a common precursor, notoamide S, by enzymes that form a bicyclo[2.2.2]diazaoctane core via a putative intramolecular hetero-Diels–Alder cycloaddition. This review provides our current understanding of the structural and stereochemical homologies and disparities of these alkaloids. Through the deployment of biomimetic syntheses, whole-genome sequencing, and biochemical studies, a unified biogenesis of both the dioxopiperazine and the monooxopiperazine families of prenylated indole alkaloids constituted of bicyclo[2.2.2]diazaoctane ring systems is presented.